


A Little Bit Farther

by Isis_McGee



Series: How Far 'verse [2]
Category: Supernatural
Genre: Anal Fingering, Bottom Dean, Dirty Talk, Dom Sam, First Time Bottom Dean, Handcuffs, Multi, Oral Sex, Plot What Plot/Porn Without Plot, Rimming, Sub Dean, Threesome - F/M/M
Language: English
Status: Completed
Published: 2015-05-11
Updated: 2015-05-11
Packaged: 2018-03-30 00:21:44
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,423
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/3916171
Author URL: https://archiveofourown.org/users/Isis_McGee/pseuds/Isis_McGee
Summary: <blockquote class="userstuff">
              <p>A brief interlude in the "As Far As You Want" 'verse where Sam and Jess teach Dean to rethink his stance on bottoming.</p>
            </blockquote>





	A Little Bit Farther

Jess didn’t bring it up a lot‒ the arrangement they had worked very well for all parties involved‒ but she thought about it every time she strapped into her harness and slicked up her silicone cock to push into Sam’s hole. She thought about it because of the way Dean’s eyes would lock onto the sight of her cock as it fucked in and out of Sam and the way he’d bite his lip at every moan Sam gave and the way he’d join in with his own moans whenever Jess start talking to Sam about how good he felt and how much she knew he loved getting fucked. Sam’s response was always to grind back into Jess and take control of the pace, but her talking was more for Dean.

But she did bring it up.

They were in Cedar Rapids, Iowa, after a run of the mill salt and burn for a jilted lover and the boys were just shucking out of their smoky shirts when Jess asked.

“Dean, will you ever tell us how you know you don’t like anal?”

It caught Dean so off guard that he dropped his arms with his shirt still only half way off. Sam paused in his movement as well, his expression mild and curious. Dean sighed and then finished taking his shirt off.

“I was 19 and there was this girl who wanted to fuck me and so I let her. It didn’t go well, okay?”

Jess snorted. “That was absolutely no explanation, but okay.” She wasn’t going to pry more.

“But why didn’t it go well?” Sam asked after a moment. There were no demands in his voice. Dean pursed his lips, the decision whether or not to explain warring on his face. He ran a hand over his face.

“She didn’t know what she was doing and I didn’t know what I was doing and it hurt, okay? It just wasn’t my thing. Having some huge fucking dick shoved up into my ass without enough lube and too hard was not my thing. And now that I’m done telling you that humiliation, I need to shower this grave dirt off of me.”

He didn’t wait for a response from either of them before slamming the bathroom door closed. The sounds of the water running started before Sam or Jess addressed each other.

“Poor Dean,” Jess said. Sam nodded a little. “So he just had a terrible experience and wrote the whole thing off?”

Sam shrugged one shoulder. “He gets like that sometimes. He holds onto stuff. He figures he has to in this line of work.”

Jess wrinkled her brow and turned to pull out a packet of baby wipes from her bag; Dean would take so long in the shower that she knew she wouldn’t have any hot water and she wasn’t that dirty to begin with. They only had two shovels still and Jess was the rock-paper-scissors queen.

“He doesn’t need to hold onto that. Not with us.” She said it quietly. She missed Sam’s shrug behind her. His face hadn’t changed when she turned back around and took two steps into his space to kiss him. “I love you.” She smiled and went on. “And I love your stupid brother, too.”

Sam couldn’t help but laugh. “Me too.”

There wasn’t any sex that night, but Jess did pull Dean into the bed with her and an already sleeping Sam and she sighed in contentment when he slung his arm over her and his hand rested on her breast. She felt him smirk, but it didn’t take him long to fall asleep. She followed soon after.

*

She brought it up again a week later while they were in Bozeman, Montana as a stop on the way to Morton, Washington where there were rumors of a clan of vampires. But this time she brought it up while Dean’s hands were cuffed behind a chair and she was kneeling between his spread legs, having just pulled off his dick. Sam was behind her shallowly rocking in and out of her cunt.

“Dean, do you trust me?” She saw him nod instead of trying to talk around the rag they’d used as a gag for him. “If you want, we can take out the gag so you can have an easier time to stop the scene if you need to.”

Dean considered for a moment, but shook his head that he could leave the gag on.

“Okay, will you just say the safe word so I know what it sounds like through the gag then?” He did, and it was fairly clear to Jess’ ears. She smiled up at him with a wicked glint still in her eyes and she wrapped her hands around his calves. “Good,” she said and yanked him forward on the chair so that his arms were stretched back and his ass was mostly hanging over the seat. Jess licked a stripe up his cock and backed off again, her hands scratching at his thighs.

Sam was still fucking into Jess, gentle and barely moving, and he draped himself over her back so he could hook his chin over her shoulder and nibble on her ear lobe before whispering to her. Sam glanced up at Dean as he did and when both of them turned smiles to Dean, Dean felt the heat of fear pooling in his belly and mixing with his arousal, heightening it.

Sam straightened up, his hands on Jess’ hips and his own hips spiraling, and didn’t look away from Dean. Dean’s eyes flicked between his and Jess’ while Jess laid open mouth kisses down his dick to his balls. She sucked one into her mouth and then the other and Dean had to throw his head back with a grunt. He felt her nose push up behind his balls and her tongue press against his perineum but it was her tongue teasing lower at his hole that made him tilt his head back up like a shot to stare at Jess. She put her hands under his knees and Sam put one on a foot and made Dean look at him.

“She’s not going to hurt you,” he reassured. “Let us make you feel good, Dean. You can stop us at any time.” Sam waited a moment, let his brother search for whatever answer he was looking for in his eyes and then went on. “Nod if you’re okay.”

Dean nodded without hesitation and he felt more than heard Jess breath out “good” and start to lick at him in earnest and shove his knees over her shoulders. Her hands were wrapped around his hips, stopping him from moving, as she swirled her tongue around his hole and nipped lightly at his cheeks and made him slick with spit.

One of Sam’s hands traveled from Jess’ hip up her back and took a brief stop to tug on her hair lightly before reaching between Dean’s bent thighs to wrap around his cock. Dean cried out and his hips twitched under Jess’ hands. She wriggled her tongue into his hole, teasing at the muscle and Dean let a long moan escape his throat. Sam was pumping his cock slowly, thumb running precome down the length and back up to join the spit drying, all his concentration on Dean.

Pleasure was written all over Dean’s face and the tension in his abs and it was ratcheted up when Sam began to pick up the pace. He smirked when he did and squeezed around Dean’s head until Dean looked him in the eye, pleasure-pain in his gaze.

“Jess is going to put just her little finger into your ass, Dean. That’s all we’re gonna do today, and you’re gonna see just how good it can be while she fingers you and licks around it. You’re all nice and slick now and your cock is so hard so I know you like it.”

Sam had barely stopped talking when Jess pressed her pinky against Dean’s hole and played in the slickness there. She moved her face so she could suck Dean’s balls into her mouth again as she pushed her finger into Dean. He gave a quiet cry that turned into a whimper of pleasure as she pushed further into him and crooked her finger. Her pinky wouldn’t reach Dean’s prostate well enough for him to see stars, but it would feel good nonetheless. It felt even better when she brought her mouth back down to suck at his rim around her finger and Sam twisted his hand around Dean’s head.

Dean gave a muffled “fuck” and Jess redoubled her efforts until his breath was coming hard through his nose.

“Tell us if you want more, Dean,” Sam said. Jess tried to press deeper into him to rub against his prostate and she brushed against it and Dean nearly shouted.  It made Sam stand, pulling out of Jess where he’d stopped moving a while ago, and rip the gag down from Dean’s mouth.

“Fuck,” was the first clear word out of Dean’s mouth. “More.”

Sam leaned down and kissed Dean hard and fast and filthy and Dean’s hips bucked back into Jess.

“How do you ask, Dean?”

“Please. Please more. Please show me how good it can feel, please, Jess, please.”

Dean had never begged them so quickly and Jess took no time obliging him, sliding her pinky out of his hole to fuck her tongue back into it to slick him up more. She reached a hand up and it was Sam who maneuvered it and told Dean “suck.” He slipped two of Jess fingers into his mouth while she licked at his hole and he moaned around them.

“I can just imagine the way you’d moan around Jess’ cock if that’s how you are with her fingers,” Sam told Dean with a slight growl in his voice. Dean’s eyes went wide and his tongued worked against Jess’ fingers to slick them up. Sam smiled indulgently. “But that’s for another day.”

Jess withdrew her fingers and trailed them down Dean’s chest lightly. She wasted no time when her hands had reached his ass again and she pushed the tips of her fingers into him. He moaned at the stretch and Sam put a gentle soothing hand on his cheek.

“You’re doing great, Dean. And you asked for this. We know how to make you feel good, remember?”

Dean was nodding even as his jaw clenched a little. It slackened when Jess started to lick around her fingers again and Sam wrapped his hand back around Dean’s cock. Jess wiggled her fingers a little, widening Dean and he groaned. She didn’t know how long it took, but Dean was stuttering out sounds of pleasure when she finally was up to her last knuckle. When she twisted her fingers so that she could rub against his prostate, those stutters turned into a drawn out cry.

“I’m going to let Jess fuck your ass more until you’re begging to come and then I’m going to lean down and suck your cock. Do you want that Dean?”

Even Jess moaned around her fingers and Dean’s ass hole at that and Dean nearly shouted. Jess sped up and pet at his spot and Dean’s hips rocked back and forth. Sam’s fingers formed a tight circle around the base of Dean’s cock.

“Please. Oh, please, fuck. Please can I come? I’ll do whatever you two want, just please let me come. I’ll do whatever. Whatever. Please. Fuck, please.” Dean was babbling and Sam shut him up with a quick, dominating kiss before he positioned himself so that he could lean over Dean’s thigh and suck his cock into his mouth. With a couple bobs of Sam’s head with hollowed cheeks, Dean was coming with a shout down his brother’s throat, his ass clenching around Jess’ fingers.

Dean was moaning still as Sam suckled at his sensitive head and Jess was pulling out of him slowly. Sam’s mouth popped off with a sound and Dean groaned again, his breathing heavy.

“Oh, fuck.”

Sam grabbed Jess’ arm and pulled her up to her feet and into his arms. Dean was moaning still as he watched Sam feed his come to Jess in their kiss before Jess wrapped her legs around Sam.

“Got the stamina for this, Sam?” she asked as he cupped his hands under her ass to hold her up. He fucked up into her and Jess smiled and cried out softly in pleasure. He wouldn’t need stamina and both of them knew it. They were both so turned on by Dean that they would come in no time. Jess decided to make it even quicker. “Can you imagine getting to fuck your brother while I fuck you, Sam? How pretty he’d look with your cock in his ass and how pretty he’d sound while you pulled all of those noises out of him?”

Sam was shoving into her hard and pulling her down onto him and Jess could feel his legs quivering. She clenched her wall muscles and pushed herself over the edge and felt Sam coming right along with her. He had the mind to stumble back two steps and sit on the bed as his orgasm continued to rush through him. Jess was still twitching her hips. The only sound in the room for a moment was the heavy breathing of all three of them.

“Where the hell you two got those mouths, I won’t ever understand,” Dean finally said, breaking the silence. Jess and Sam both turned to look at him. “I felt my dick trying to get hard again.”

Jess laughed and she maneuvered off of Sam gingerly. Her legs felt a little numb from kneeling for so long still, but she wanted to uncuff Dean and get the three of them cleaned up.  She helped him stand and pushed him towards the bed gently. He went and flopped down onto his back next to Sam while Jess padded to the bathroom. She looked over her shoulder at the two of them and saw Sam smiling at Dean and carding a hand through his hair whole Dean pretended to look annoyed.

“So, you rethink your position about things going up your ass?” she teased Dean before she stepped into the bathroom with a washrag in her hand. Dean tilted his chin up to look at her after glancing at Sam. He had a grin on his face.

“Hell, yes.”


End file.
